By the time Lester “George Baby Face Nelson” Gillis was learning to run rum in the Chicago suburbs, and John Dillinger was serving time for armed robbery, the Winona booze racket was in full swing.

The city is seldom mentioned in the historical accounts of America’s most notorious criminal era — there were no big bank robberies, shootouts or kidnappings. But many Winonans were certainly willing to take part in an illicit business that lined the gangsters’ pockets.

When Prohibition started in 1919, the city had 42 saloons. Just a few years later, a thirsty Winonan could find a drink in as many as 200 speakeasies, many operating in the open. The Cozy Corner on West Fifth Street and the Unlucky Seven on Third Street— what is Gabby’s today — served “home brew” made in Winona. Some private living rooms turned into taverns come nightfall.

An investment of just 5 cents could make $5 in profit on the black market, and it wasn’t long before the city’s bathtubs were filled with gin and farmyard stills overflowed with whiskey. Winona became known throughout the Midwest as an “open town,” where police largely turned a blind eye and graft kept the liquor flowing.

Its location on the booze pipeline from Chicago to St. Paul meant Winona was a popular waypoint for the underworld elite. Newspaper reports tell of bullet-riddled cars found in Winona County ditches, empty except for the lingering scent of their cargo.

“(Gangsters) moved through the area quite a bit,” says Chad Lewis, author of “The Minnesota Road Guide to Gangster Hot Spots.” “And when they came to town, you knew exactly who they were because of their clothes and cars.”

That, and what they ate at the county jail.

On the rare occasions Winona police made arrests, the gangsters

unfortunate enough to be caught

ordered their meals from Winona’s finer hotels and restaurants. It wasn’t unusual to see waiters carrying trays into the jail at mealtime.

A chance to rub shoulders with the country’s most notorious criminals kept the speakeasies hopping, Lewis said. One club in particular, the Oaks in Minnesota City, was rumored to be a mob hangout, said Walt Bennick, an archivist at the Winona County Historical Society.

Other clubs and speakeasies catered to the everyday Winonan. “Thousands of Winona residents who ordinarily would not have even thought of breaking a municipal ordinance were found to have no qualms about participating in the most flagrant, widespread violation of the highest law of the land,” according to an abridged Winona Daily News story published in 1955.

But by the late 1920s, a decade of excess had drawn the attention of federal officials in St. Paul and Washington, D.C.

The nation’s top Prohibition official, James Doran, grew up in Winona, where his father was a Methodist minister. He was named federal commissioner of Prohibition in 1927, and after a visit to his boyhood home the next year, he was rumored to be appalled at the rampant lawlessness. More federal liquor cases were filed against Winonans in the 18 months after his visit than had been in the entire decade prior. Federal officials conducted 25 raids and made 31 arrests alone in June 1928. Many of the arrested ended up in the federal prison at Leavenworth, Kan.

The most significant crackdowns began in 1929, when four federal agents came to Winona as part of a two-month investigation into dry-laws violations in the city. When word got out that the feds were in town, several hundred people gathered to wait for them on Mankato Avenue, according to reports in the Winona Republican-Herald, the grandfather paper of the Winona Daily News. The agents were chased away, rocks flying behind them.

The feds pledged to return, and on Aug. 26, 1929, a busload of 35 agents disguised as picnickers rolled into Winona. Once again, word of their arrival spread quickly. Only this time, the crowd was 500 people. The mob attacked the bus near Mankato Avenue and slashed its tires. One woman was knocked unconscious. It took police five hours to clear the streets. The feds rounded up 17 Winonans, and had to cling to the side of the bus as it rambled toward the jail.

“Knock, Knock, Knock, the Feds are Raiding,” read the banner headlines in next editions of the Republican-Herald. When police later investigated the vandalism, they couldn’t find a single witness to the incident.

Following the Mankato raids, the feds in St. Paul named a special division chief tasked specifically with drying out Winona. Karl “Baby Face” Neurenburg promised to raid the city once a week. In November, he padlocked 23 speakeasies on a single day. Thousands of gallons of home brew were destroyed.

But the raids did little to quell Winona’s appetite for booze. On Oct. 22, 1930, two Winona men were arrested trying to steal 310 gallon tins of seized whiskey stored at the La Crosse, Wis., home of a federal agent. The next year, a rum runner was gunned down in St. Charles.

By 1932, the city — and even some public officials — were fed up. The city was still being raided regularly, even as an underworld element continued to operate. Scores of otherwise innocent Winonans were in federal prisons. On May 14, Mayor James B. Rice led a parade against Prohibition through the city streets.

Popular opinion was beginning to shift in other parts of the country, as well. Herbert Hoover’s G-men had shifted the public’s perception of the gangsters from likeable celebrities to public enemies, Lewis said. The feds were getting better at tracking them, and the gangsters were driven underground by big rewards and intensifying violence.

Prohibition ended Dec. 5, 1933, and within a year, John Dillinger and Baby Face Nelson were dead. Winona’s illicit booze market dried up, and the feds went back to St. Paul.

“I think deep down, everyone wanted it to end,” Lewis said. “The lifestyle got to be too much.”